Sexploration: Losing my virginity at 27

Posted on March 31, 2016

I let a near stranger give me an orgasm in the front seat of my car.

I never thought that would happen to me—that I would act on my instinct, squash anxiety, and actually enjoy the rush of getting a hand job in a parking lot where someone might see. But then it happened; I didn’t overthink it, I just did it—and I enjoyed it. My boyfriend will be so proud.

Let me back up a little.

A year ago, I was a virgin—I lost it days before my 28th birthday. (I KNOW. It was a momentous occasion.) At the time everyone thought I was crazy because I jumped headfirst into a relationship with my boyfriend, who I met online, and we’ve had unexplainable connection since our first encounter. The first time we ever talked, before we even met in person, I told him I was a virgin. He was very quiet, then he laughed and said, “I’m far from that” and preceded to tell me he lived an active lifestyle as a switch in BDSM. I guess a normal virgin girl maybe would’ve run away—but it excited me. I’d read Fifty Shades and I liked that; plus it meant he had experience. It’d be worth it to see what happened. (It was.)

A year later and we’re still together in a relationship. I know he never imagined that he’d be 1) monogamous or 2) with a vanilla virgin, but it works because we communicate openly.

I didn’t plan to be a 27-year-old virgin; it just happened.

I grew up religious, even went to a religious college, and it was pounded into my head that sex was “for marriage”. You weren’t supposed to ask questions, to masturbate, to think impure thoughts, watch porn, or put anything into your head or heart that was immoral. I always struggled with that, even though I never told anyone. I’d always been curious about sex; I had questions; I watched porn sometimes—all natural things that I was made to feel were bad. I had curiosities but never acted on anything because of fear, and even after I walked away from the church part of me still believed it. Then I met him, sex happened, and my eyes were opened—and now I know I missed out for many years.

Being with someone who’s really experienced and lives BDSM, is a totally overwhelming but intriguing experience. And frankly, my guy is good at sex—but over the last year I have felt inferior. In the bedroom, he’s the one who takes charge and leads—and even when I have an idea, I don’t voice it. What do I know? He has all the experience. (I say it’s like trying to drive a car when I’ve never been in one before.)

I don’t have sexual confidence.

I want to.

I’ve learned that I enjoy sex. A lot. I crave more experience, knowledge, practice, and challenges. I want to explore his world; I want to explore my own curiosities, urges, and intrigues. I want to be in control, to dominate and to take charge of the bedroom. I want all of that. I finally admitted to him that I want to gain confidence, to discover myself sexually and to explore. My guy was very, very excited about it, except one problem: he’s in another country until September 2016.

After discussions with him about who, what, how and rules (no V-in-P, no feelings, no making out) and four months of me thinking about it, I am finally about to go on a sex discovery and exploration. (A Sexploration, if you will.) And since he’s gone for five-to-seven more months, on top of the four he’s already been away, I’m doing it with other people.

That’s how I ended up in the front seat of my car with a near stranger…and how I had my first really great orgasm in four months.

In my whole life I never thought I’d be curious enough or brave enough to take charge of this desire. To embrace my own needs. Yet here I am. I’m just starting this journey to learn how to express what I want sexually, be dominant in my own sex life, and experiment with taboo things like bondage and anal play (we’ll see how all that goes) all with someone(s) who is not my boyfriend.

It’s pretty exciting for me.

I want to gain confidence for myself and get to know what I like and what I don’t. I want to do every single thing I was told I could never do because it was “sinful.” I want to be brave and independent. I want to rack up skills to shock him when we reunite. I’m learning sex is fun, empowerment is good, and knowing your own sexuality is a positive thing—and since I will be 29 in two weeks, it’s about damn time.